This invention relates to novel pyrazole sulfonamides. The compounds of this invention and their agriculturally suitable salts, are useful as agricultural chemicals, e.g. plant growth regulants and herbicides. As herbicides, the compounds of this invention have both preemergent and/or postemergent utility. The invention is also intended to cover the use of these chemicals in the form of compositions.
Herbicidal sulfonylureas are claimed in U.S. Pat. Nos. 4,127,405 and 4,167,719.
EP-A-79,683 discloses herbicidal sulfonylureas including those of formula ##STR1## wherein Q is O, S or SO.sub.2 ;
R.sub.2 is H or C.sub.1 -C.sub.3 alkyl; PA0 R.sub.3 is H or CH.sub.3 ; and PA0 R.sub.4 is H or CH.sub.3. PA0 B and C are independently H, halogen, C.sub.1 -C.sub.8 alkyl, CO.sub.2 R, SO.sub.2 NR.sub.4 R.sub.5, etc. PA0 D is H or C.sub.1 -C.sub.8 alkyl; PA0 X and Y are independently H, halogen, C.sub.1 -C.sub.8 alkyl, C.sub.1 -C.sub.8 alkoxy, etc.; and PA0 Z is C--R.sub.8 or N. PA0 R.sub.2 is H or CH.sub.3 ; PA0 R.sub.3 is R.sub.4, SR.sub.4, SO.sub.2 R.sub.4, OR.sub.4, C(O)R.sub.4, C(O)OR.sub.4, (C(O)).sub.2 OR.sub.4, (CO).sub.2 R.sub.4, C(O)NR.sub.5 R.sub.6, C(O)NRA, C(S)SR.sub.4, NR.sub.5 R.sub.6, OH, CN, P(O)R.sub.7 R.sub.8, P(S)R.sub.7 R.sub.8, Si(CH.sub.3).sub.2 R.sub.9, J or C(O)J; PA0 R.sub.4 is C.sub.1 -C.sub.10 alkyl, C.sub.2 -C.sub.10 alkoxyalkyl, C.sub.2 -C.sub.10 alkenyl, C.sub.2 -C.sub.10 epoxyalkyl, C.sub.2 -C.sub.10 alkynyl, C.sub.3 -C.sub.6 cycloalkyl, C.sub.4 -C.sub.7 cycloalkylalkyl or ##STR8## when R.sub.4 is C.sub.3 -C.sub.6 cycloalkyl or C.sub.4 -C.sub.7 cycloalkylalkyl it may optionally be substituted by C.sub.1 -C.sub.4 alkyl, 1 to 3 atoms of Cl or F or 1 Br; when R.sub.4 is C.sub.1 -C.sub.10 alkyl, C.sub.2 -C.sub.10 alkenyl or C.sub.2 -C.sub.10 alkynyl it may optionally be substituted by one or more halogens and/or by (R.sub.11).sub.p, provided that when p is 2, the values of R.sub.11 may be identical or different; PA0 p is 1 or 2; PA0 R.sub.5 is H or C.sub.1 -C.sub.4 alkyl; PA0 R.sub.6 is H, C.sub.1 -C.sub.10 alkyl, C.sub.1 -C.sub.10 haloalkyl, C.sub.2 -C.sub.10 alkenyl, C.sub.2 -C.sub.10 alkynyl, C.sub.3 -C.sub.6 cycloalkyl or ##STR9## R.sub.7 and R.sub.8 are independently C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 alkoxy or C.sub.1 -C.sub.4 alkylthio; PA0 R.sub.9 is C.sub.1 -C.sub.10 alkyl, benzyl or ##STR10## R.sub.10 is H, F, Cl, Br, CH.sub.3, OCH.sub.3, NO.sub.2, CN, SCH.sub.3, SO.sub.2 CH.sub.3 or CF.sub.3 ; PA0 R.sub.11 is OR.sub.6, OC(O)R.sub.6, P.sup.+ R.sub.9 R.sub.13 R.sub.14, P.sup.+ (C.sub.6 H.sub.5).sub.3, OC(O)NR.sub.5 R.sub.6, OSO.sub.2 R.sub.6, OP(O)R.sub.7 R.sub.8, P(O)R.sub.7 R.sub.8 OP(S)R.sub.7 R.sub.8, P(S)R.sub.7 R.sub.8, OSi(CH.sub.3).sub.2 R.sub.9, Si(CH.sub.3).sub.2 R.sub.9, SR.sub.6, SOR.sub.6, SO.sub.2 R.sub.6, SCN, CN, SP(O)R.sub.7 R.sub.8, SP(S)R.sub.7 R.sub.8, N.sup.+ R.sub.5 R.sub.6 R.sub.9, NR.sub.5 R.sub.6, NR.sub.5 C(O)R.sub.6, NR.sub.5 C(O)OR.sub.6, NR.sub.5 C(O)NR.sub.5 R.sub.6, NR.sub.5 SO.sub.2 R.sub.6, NR.sub.5 P(O)R.sub.7 R.sub.8, NR.sub.5 P(S)R.sub.7 R.sub.8, NO.sub.2, C(O)R.sub.6, C(O)OR.sub.6, C(O)NR.sub.5 R.sub.6, SeR.sub.6, naphthyl, J, ##STR11## R.sub.12 is H, F, Cl, Br, CH.sub.3, ##STR12## R.sub.13 and R.sub.14 are independently C.sub.1 -C.sub.3 alkyl; J is a 5- or 6-membered aromatic heterocycle, a 5- or 6-membered dihydroaromatic heterocycle or a 5- or 6-membered tetrahydroaromatic heterocycle which contains 1-4 heteroatoms selected from 0-1 oxygen atoms, 0-1 sulfur atoms and/or 0-4 nitrogen atoms and these heterocycles may optionally be substituted by 1-4 CH.sub.3, 1-2 OCH.sub.3, SCH.sub.3, Cl, N(CH.sub.3).sub.2 or CN groups or J is a 5- or 6-membered lactone, lactam or cycloalkanone which may optionally be substituted by 1-4 CH.sub.3 groups; PA0 A is ##STR13## X is H, C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 alkoxy, C.sub.1 -C.sub.4 haloalkoxy, C.sub.1 -C.sub.4 haloalkyl, C.sub.1 -C.sub.4 haloalkylthio, C.sub.1 -C.sub.4 alkylthio, halogen, C.sub.2 -C.sub.5 alkoxyalkyl, C.sub.2 -C.sub.5 alkoxyalkoxy, amino, C.sub.1 -C.sub.3 alkylamino, di(C.sub.1 -C.sub.3 alkyl)amino or C.sub.3 -C.sub.5 cycloalkyl; PA0 Y is H, C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 alkoxy, C.sub.1 -C.sub.4 haloalkoxy, C.sub.1 -C.sub.4 haloalkylthio, C.sub.1 -C.sub.4 alkylthio, halogen, C.sub.2 -C.sub.5 alkoxyalkyl, C.sub.2 -C.sub.5 alkoxyalkoxy, amino, C.sub.1 -C.sub.3 alkylamino, di(C.sub.1 -C.sub.3 alkyl)amino, C.sub.3 -C.sub.4 alkenyloxy, C.sub.3 -C.sub.4 alkynyloxy, C.sub.2 -C.sub.5 alkylthioalkyl, C.sub.2 -C.sub.5 alkylsulfinylalkyl, C.sub.2 -C.sub.5 alkylsulfonylalkyl, C.sub.1 -C.sub.4 haloalkyl, C.sub.2 -C.sub.4 alkynyl, azido, cyano, ##STR14## N(OCH.sub.3)CH.sub.3 ; m is 2 or 3; PA0 Q.sub.1 and Q.sub.2 are independently O or S; PA0 R.sub.a is H or C.sub.1 -C.sub.3 alkyl; PA0 R.sub.b and R.sub.c are independently C.sub.1 -C.sub.3 alkyl; PA0 Z is CH, N, CCH.sub.3, CC.sub.2 H.sub.5, CCl or CBr; PA0 Y.sub.1 is O or CH.sub.2 ; PA0 X.sub.1 is CH.sub.3, OCH.sub.3, OC.sub.2 H.sub.5 or OCF.sub.2 H; PA0 X.sub.2 is CH.sub.3, C.sub.2 H.sub.5 or CH.sub.2 CF.sub.3 ; PA0 Y.sub.2 is OCH.sub.3, OC.sub.2 H.sub.5, SCH.sub.3, SC.sub.2 H.sub.5, CH.sub.3 or CH.sub.2 CH.sub.3 ; PA0 X.sub.3 is CH.sub.3 or OCH.sub.3 ; and PA0 Y.sub.3 is H or CH.sub.3 ; PA0 1. when X is halogen, then Z is CH and Y is OCH.sub.3, OC.sub.2 H.sub.5, NH.sub.2, NHCH.sub.3, N(CH.sub.3).sub.2 or OCF.sub.2 H; PA0 2. when R.sub.3 is R.sub.4, then R.sub.4 is other than C.sub.1 -C.sub.3 alkyl or CF.sub.2 H; PA0 3. the total number of carbon atoms in R.sub.3 does not exceed 13; PA0 4. when R.sub.6 is H, then R.sub.11 is other than SOR.sub.6, SO.sub.2 R.sub.6, OSO.sub.2 R.sub.6 or NR.sub.5 CO.sub.2 R.sub.6 ; and PA0 5. when X or Y is OCF.sub.2 H, then Z is CH PA0 A is A-1; PA0 X is CH.sub.3, OCH.sub.3, OCH.sub.2 CH.sub.3, Cl, F, Br, OCF.sub.2 H, CH.sub.2 F, CF.sub.3 or cyclopropyl; PA0 Y is H, C.sub.1 -C.sub.3 alkyl, OCH.sub.3, OC.sub.2 H.sub.5, CH.sub.2 OCH.sub.3, NH.sub.2, NHCH.sub.3, N(OCH.sub.3)CH.sub.3, N(CH.sub.3).sub.2, C.sub.2 H.sub.5, CF.sub.3, SCH.sub.3, OCH.sub.2 CH.dbd.CH.sub.2, OCH.sub.2 C.tbd.CH, OCH.sub.2 CF.sub.3, CN, N.sub.3, OCH.sub.2 CH.sub.2 OCH.sub.3, CH.sub.2 SCH.sub.3, ##STR15## or QCF.sub.2 T; Q is O or S; and PA0 T is H, CHClF, CHBrF or CHFCF.sub.3 ; PA0 N-[(4,6-dimethoxypyrimidin-2-yl)aminocarbonyl]-5-(2-fluoroethyl)-2,5,6,7-te trahydro-2-methylpyrazolo[3,4-e][1,2]thiazine-3-sulfonamide, 4,4-dioxide; PA0 5-butyl-N-[(4,6-dimethoxypyrimidin-2-yl)aminocarbonyl]-2,5,6,7-tetrahydro-2 -methylpyrazolo[3,4-e][1,2]thiazine-3-sulfonamide, 4,4-dioxide; and PA0 5-acetyl-2,5,6,7-tetrahydro-N-[(4-methoxy-6-methyl-1,3,5-triazin-2-yl)amino carbonyl]-2-methylpyrazolo[3,4-e]thiazine-3-sulfonamide, 4,4-dioxide.
EP-A-107,979 discloses, in part, herbicidal sulfonylureas of formula ##STR2## wherein J is, among other values, ##STR3## and A is a heterocyclic pyrimidine, triazine, triazole or a derivative thereof.
South African Patent Application No. 83/5165 discloses herbicidal sulfonylureas of the formula ##STR4## wherein A is an unsubstituted or substituted bridge of 3 or 4 atoms which contains 1 or 2 oxygen, sulfur or nitrogen atoms and, together with the linking carbon atom, forms a non-aromatic 5- or 6-membered heterocyclic ring system, with the proviso that two oxygen atoms are separated by at least one carbon atom and that oxygen and sulfur atoms are only linked to each other if the sulfur atom takes the form of the --SO-- or SO.sub.2 -- group.
EP-A-87,780 (published 9/7/83) claims pyrazole sulfonylureas of formula ##STR5## wherein A is H, C.sub.1 -C.sub.8 alkyl or optionally substituted phenyl;
The presence of undesired vegetation causes substantial damage to useful crops, especially agricultural products that satisfy man's basic food and fiber needs, such as cotton, rice, corn, wheat and the like. The current population explosion and concommitant world food and fiber shortage demand improvements in the efficiency of producing these crops. Preventing or minimizing loss of a portion of such valuable crops by killing or inhibiting the growth of undesired vegetation is one way of improving this efficiency.
A wide variety of materials useful for killing or inhibiting (controlling) the growth of undesired vegetation is available; such materials are commonly referred to as herbicides. The need still exists however, for more effective herbicides.